
Apartment vacation rentals in South Loop
Find and book unique apartments on Airbnb
Top-rated apartment rentals in South Loop
Guests agree: these apartments are highly rated for location, cleanliness, and more.

Professional's Playground (Fitness Center • Sauna)
Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 2 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. Within walking distance are world famous attractions including: Millennium Park, The Bean, Navy Pier, Riverwalk, Soldier Field, The Field Museum, and more. Additionally, guests are merely a couple blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city.

Upscale High-Rise Apt · Rooftop Pool + Views
Stay in this brand-new 2025 apartment with luxury amenities. Perfect for work or leisure, it offers everything you need for a comfortable stay. Building Amenities: - 24/7 concierge & secure entry - Rooftop pool & gym with skyline views - Rooftop lounge with a fireplace - Steps from grocery stores & restaurants - Paid parking nearby Unit Highlights: - Stunning views of the city - Work from home space - In-unit washer & dryer - Fully equipped kitchen - Fast WiFi - Modernly designed interior

Dtown Penthouse 11+Parking, Gym, Pvt Patio
Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: ✅ Central location near Grant Park, Art Institute, The Bean, Soldier Field, & more! ✅ 1 Free parking pass ✅ FAST WIFI ✅ En-suite Laundry ✅ The Lake & Park are only 2 blocks away ✅ KING beds ✅ Private Rooftop Deck w/ stunning views ✅ Amenity Floor (Gym, Lounge, Doggy Park) ✅ 1 block from Red "L" subway

Unmatched Urban Retreat Close to 18th Strip & Loop
This stylish Airbnb in the very popular Pilsen neighborhood is perfect for small and large travel groups. There are 2 bedrooms with queen size beds, and the couch folds out for an additional sleeping area. The 2 full bathrooms will have everything you need to get ready to hit the town. The tall ceilings make this space for larger than life, and the unique décor gives this Airbnb a great urban feel. The fully equipped kitchen and updated appliances are perfect for those quiet nights in.

South Loop | Rooftop With In & Out Parking | 3
Enjoy a stylish experience at this centrally located place! This stunning 1,000 sq. ft. modern 2-bedroom, 2-bathroom unit is perfect for corporate travelers and families looking for a chic escape in downtown Chicago 🏡💼 🔥 Rooftop Patio W/ BBQ 🍖☀️ 🏊 Rooftop Pool 🌆 🚗 Free In/Out Parking (5-Min Walk to Garage) 🅿️ 🛏️ 2 Bedrooms | 2 Bathrooms 🚿 🛌 2 Queen Beds 🛏️ 💨 1 Inflatable Airbed 🛌 👶 Portable Crib (For Mini Travel Companion) 🎬 Netflix, Hulu, Disney+ & Prime Included 📺

Kasa | Spectacular City Views | Chicago
When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

South Loop 3BD 2BA Condo with Balcony and Parking
Stay in the heart of Chicago’s South Loop at this spacious 3-bedroom, 2-bath condo on Michigan Avenue. Enjoy easy access to Grant Park, Museum Campus, Soldier Field, McCormick Place, and the Lakefront Trail, with CTA trains and buses just steps away. This modern, walkable home features updated bathrooms and kitchen with new fixtures, hardwood floors throughout, a nice front deck, and an in-unit full-sized washer and dryer—perfect for families, groups, or business travelers.

Spacious 1-bedroom South Loop Loft I Sleep 5
Enjoy Chicago in our modern & spacious 1-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!

1BR South Loop Loft I SuperHost + Top Rated!
Enjoy Chicago in our modern & spacious 1-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!

LIVN West Loop Chicago Queen Studio Apartment
Experience modern city living at LIVN West Loop Chicago, a stylish loft-style apartment studio at 555 W Jackson Blvd in one of the city’s most connected neighborhoods. This newly renovated studio features a full kitchen, in-unit washer and dryer, and clean, modern interiors. Walk to Union Station and Willis Tower. You are minutes from top dining, offices, and transit, ideal for business trips, weekend stays, or longer visits.

Level Junior Two Bedroom Suite | Fulton Market
Two bedroom, two bathroom suite featuring a king bed, queen bed, and sofa bed. Maximum occupancy is 4. Enjoy access to over 32,000 sq ft of unrivaled lifestyle amenities, including a seasonal outdoor pool, a relaxing hot tub, and a state-of-the-art fitness center. Take in stunning views of the Chicago skyline from our Cloud Lounge, grill meals at the BBQ stations, and enjoy movie or game nights in the media room.

South Loop Studio Hotel (309)
Stay in the center of the action in this one-of-a-kind place! You’ll be within walking distance of Chicago's most iconic landmarks. ⚠️ Please Note: Our elevator is currently undergoing repairs. All guests will need to use the stairs to access the unit. We apologize for the inconvenience and appreciate your understanding as we maintain our unique space!
Popular amenities for South Loop apartment rentals
Weekly apartment rentals

Archways at the Lincoln Park Zoo 2bed/2ba

1BR Near South Loop | Mccormick Place

Chicago Luxurious 3BR Near McCormick Place!

Sleek 1BR Apartment w/ In-unit Laundry

Modern 2BR Unit w Patio & Gym Near McCormick Place

Stylish Hyde Park/Kenwood Brownstone Garden Apt

Luxury Living in Bronzeville with Massive Roofdeck

The Luxe Haven | 1BR | Near City | Free Parking
Private apartment rentals

Gold Coast Luxury: 2BR with Sweeping City Vistas

Roomy 1BR Apt w/ In-Unit Laundry

Lavish 2BR/2BA Loft I Next to Grant Park & Museums

Downtown Penthouse Lake Views #1|Gym, Parking

Boho Chic Oasis with Private Parking

The South Loop Reserve I Sleep 6 I Top Rated

The Executive's Escape (Fitness Center • Sauna)

Brilliant 2BR/2BA Loft I SuperHost I Sleep 6
Apartment rentals with a hot tub

Super Paradise+65 Amenities*Downtown 15 Min

Luxury 3BD Penthouse – Private Patio+Skyline Views

Skyline Oasis: City & Lake Views

Modern 4BR West Town Duplex | Best for LongStays

Spacious 1BR | 1 Garage Parking | Nightlife nearby

Belmont Pleasures - hot tub / arcade gaming room

420 friendly apt with 2 queens,1 full,1 twin bed

Executive Retreat Gym Sauna Whirlpool Steam Shower
When is the best time to visit South Loop?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$28,034 GYD | G$31,382 GYD | G$38,286 GYD | G$40,169 GYD | G$49,165 GYD | G$52,512 GYD | G$55,023 GYD | G$52,303 GYD | G$46,654 GYD | G$54,604 GYD | G$40,378 GYD | G$35,148 GYD |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Quick stats about apartment rentals in South Loop

Total vacation rentals
Explore 380 vacation rentals in South Loop

Nightly prices starting at
South Loop vacation rentals start at G$8,368 GYD per night before taxes and fees

Verified guest reviews
Over 17,120 verified reviews to help you choose

Family-friendly vacation rentals
240 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 100 rentals that welcome pets

Vacation rentals with a pool
110 properties feature pools

Rentals with dedicated workspaces
260 properties have a dedicated workspace

Wi-Fi availability
380 of South Loop vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across South Loop rentals

4.7 Average rating
South Loop stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Rentals with a patio South Loop
- Rentals with lake access South Loop
- Rentals with a hot tub South Loop
- Pet-friendly rentals South Loop
- Rentals with a fireplace South Loop
- Family-friendly rentals South Loop
- Rentals with an EV charger South Loop
- Rentals with a sauna South Loop
- Fitness-friendly rentals South Loop
- Rentals with a washer and dryer South Loop
- Rentals with pools South Loop
- Smoking-friendly rentals South Loop
- Rentals with outdoor seating South Loop
- Condo rentals South Loop
- Rentals with a fire pit South Loop
- Apartment rentals Chicago
- Apartment rentals Cook County
- Apartment rentals Illinois
- Apartment rentals United States
- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Grant Park
- Navy Pier
- Chicago River Walk
- Soldier Field
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- The Field Museum
- Guaranteed Rate Field
- Union Park
- Lincoln Park Zoo
- University of Chicago
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- Museum of Science and Industry
- Washington Park Zoo
- Illinois Beach State Park
- Loyola University Chicago





